Self‐standing chiral electroactive synthetic membranes are presented, prepared by oxidative electrooligomerization of a thiophene‐based "inherently chiral" electroactive monomer on indium tin oxide ITO or fluorine doped tin oxide FTO electrodes, followed by detachment of the electrodeposited thin films in aqueous solution. The membranes, possibly mesoporous, consist of a mixture of open and cyclic "inherently chiral" oligomers, i.e. in which both chirality and electroactivity originate from the same source, the main conjugated backbone featuring a tailored torsion; such a combination can afford outstanding chirality manifestations. The electrosynthesis conditions significantly modulate the oligomer distribution. Racemate films are compared to enantiopure ones. Circular dichroism confirms that (R)‐ or (S)‐ enantiopure films are obtained starting from the corresponding (R)‐ or (S)‐ enantiopure monomers. Reliable transmembrane potential readings are obtained in preliminary tests in ion‐selective electrode (ISE)‐like setups, consistent with those predicted considering the membrane features, a first step towards extension of the protocol to chiral experiments.

Self‐standing membranes consisting of inherently chiral electroactive oligomers: electrosynthesis, characterization and preliminary tests in potentiometric setups / S. Arnaboldi, D. Vigo, M. Longhi, F. Orsini, S. Riva, S. Grecchi, E. Giacovelli, V. Guglielmi, R. Cirilli, G. Longhi, G. Mazzeo, T. Benincori, P.R. Mussini. - In: CHEMELECTROCHEM. - ISSN 2196-0216. - 6:16(2019 Aug 16), pp. 4204-4214.

Self‐standing membranes consisting of inherently chiral electroactive oligomers: electrosynthesis, characterization and preliminary tests in potentiometric setups

S. Arnaboldi
Primo
;
M. Longhi;F. Orsini;S. Grecchi;V. Guglielmi;G. Mazzeo;P.R. Mussini
2019

Abstract

Self‐standing chiral electroactive synthetic membranes are presented, prepared by oxidative electrooligomerization of a thiophene‐based "inherently chiral" electroactive monomer on indium tin oxide ITO or fluorine doped tin oxide FTO electrodes, followed by detachment of the electrodeposited thin films in aqueous solution. The membranes, possibly mesoporous, consist of a mixture of open and cyclic "inherently chiral" oligomers, i.e. in which both chirality and electroactivity originate from the same source, the main conjugated backbone featuring a tailored torsion; such a combination can afford outstanding chirality manifestations. The electrosynthesis conditions significantly modulate the oligomer distribution. Racemate films are compared to enantiopure ones. Circular dichroism confirms that (R)‐ or (S)‐ enantiopure films are obtained starting from the corresponding (R)‐ or (S)‐ enantiopure monomers. Reliable transmembrane potential readings are obtained in preliminary tests in ion‐selective electrode (ISE)‐like setups, consistent with those predicted considering the membrane features, a first step towards extension of the protocol to chiral experiments.
self-standing electroactive chiral membranes; inherent chirality; enantiopure membranes; chiral thiophene-based oligomers; potentiometric setups
Settore CHIM/01 - Chimica Analitica
Settore CHIM/02 - Chimica Fisica
   Enhancing VINCE (Versatile INherently Chiral Electrochemistry)
   FONDAZIONE CARIPLO
   2016-0923

   Fondo per il finanziamento delle attività base di ricerca - DIPARTIMENTO DI CHIMICA
   MINISTERO DELL'ISTRUZIONE E DEL MERITO
16-ago-2019
24-lug-2019
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/665167
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